53402-10-1

Basic information

• Product Name: (1R)-(-)-THIOCAMPHOR
• Synonyms: (1R)-(-)-THIOCAMPHOR;(1r)-(-)-1,7,7-trimethylbicyclo[2.2.1]heptane-2-thione;(1R,4R)-1,7,7-Trimethylbicyclo[2.2.1]heptane-2-thione;(1R)-(-)-Thiocamphor
• CAS NO: 53402-10-1
• Molecular Formula: C₁₀H₁₆S
• Molecular Weight: 168.3
• Product Categories: Bicyclic Monoterpenes;Biochemistry;Terpenes
• Mol File: 53402-10-1.mol

Chemical Properties

• Melting Point: 136-138 °C(lit.)
• Boiling Point: 228-230 °C(lit.)
• Flash Point: 81.7 °C
• Appearance: /
• Density: 0.9691 (rough estimate)
• Vapor Pressure: 0.107mmHg at 25°C
• Refractive Index: 1.6500 (estimate)
• CAS DataBase Reference: (1R)-(-)-THIOCAMPHOR(CAS DataBase Reference)
• NIST Chemistry Reference: (1R)-(-)-THIOCAMPHOR(53402-10-1)
• EPA Substance Registry System: (1R)-(-)-THIOCAMPHOR(53402-10-1)

Safety Data

• Hazard Codes: F,Xi
• Statements: 11-36/37/38
• Safety Statements: 16-26-36
• RIDADR: UN 1325 4.1/PG 3
• WGK Germany: 3
• HazardClass: 4.1
• PackingGroup: III
• Hazardous Substances Data: 53402-10-1(Hazardous Substances Data)

Usage

Purification Methods

It forms red prisms from EtOH and sublimes under vacuum. It possesses a sulfurous odour and is volatile like camphor. [Sen J Indian Chem Soc 12 647 1935, Sen J Indian Chem Soc 18 76 1941.] The racemate crystallises from *C6H6 and has m 145o [138.6-139o, White & Bishop J Am Chem Soc 62 10 1940]. [Beilstein 7 III 419.]

InChI:InChI=1/C10H16S/c1-9(2)7-4-5-10(9,3)8(11)6-7/h7H,4-6H2,1-3H3/t7-,10+/m1/s1

Upstream product

• 31180-79-7 N-nitrocaphorimine 
• 5391-78-6 bornane-2-thiol 
• 76-22-2 Camphor 
• 736109-58-3 1,7,7-trimethyl-bicyclo[2.2.1]heptan-2-one 
• 770-53-6 bornan-2-one-hydrazone 
• 72995-90-5 camphor pyrrolidinoenamine 
• 464-49-3 (1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one 
• 126314-33-8 di-((1R)-bornyl)-disulfide 
• 59121-52-7 (1R)-(+)-thiocamphor S-oxyde 
• 464-49-3 (1R)-1,7,7-trimethyl-bicyclo[2.2.1]heptan-2-one 

Downstream Products

• 73041-53-9 (+/-)-2-Diphenylmethylencamphen 
• 736109-58-3 1,7,7-trimethyl-bicyclo[2.2.1]heptan-2-one 
• 2767-84-2 Camphorquinone 
• 76013-16-6 3-endo-(phenylseleninyl)camphor 
• 50404-35-8 thiocamphor S-oxide 
• 110212-62-9 diethyl (E)-2,3-diphenylmaleate 
• 119593-83-8 Phenyl-(1,7,7-trimethyl-bicyclo[2.2.1]hept-2-en-2-ylsulfanyl)-acetic acid ethyl ester 
• 59056-08-5 1,7,7-Trimethyl-2-phenylmethanesulfonyl-bicyclo[2.2.1]hept-2-ene 
• 70136-66-2 thiobenzoic acid S-born-2-en-2-yl ester 
• 70136-68-4 4-Methoxy-thiobenzoic acid S-(1,7,7-trimethyl-bicyclo[2.2.1]hept-2-en-2-yl) ester 
• 59056-13-2 1-(4-Bromo-phenyl)-2-(1,7,7-trimethyl-bicyclo[2.2.1]hept-2-ene-2-sulfonyl)-ethanone 
• 2792-42-9 (R,R)-camphor oxime 
• 133113-64-1 C₁₇H₂₀N₂O₂S₂ 
• 619-72-7 4-nitrobenzonitrile 

Relevant articles and documents

Enantiospecific synthesis of substituted 1-norbornyl trifluoromethanethiosulfonates and 1-norbornanethiols

New homochiral 1-norbornylthiotriflates 6 and 7 and 1-norbornanethiols 8 and 9 are easily prepared starting from naturally occurring 2-norbornanones 1. The key step is the reaction of chiral 2-norbornanethiones 2 with Tf2O under mild conditions.

Reactions of cycloaliphatic thioketones and their Oxo analogues with lithiated methoxyallene: A new approach to vinylthiiranes

Admantanethione smoothly reacted with lithiated methoxyallene at low temperatures yielding the expected allenyl-substituted thiolate, which upon aqueous work-up underwent spontaneous 1,3-cyclization to afford a hitherto unknown methoxy-substituted vinylth

Formation of kinetically stabilized dithiiranes by treating thione S-oxides bearing a bulky substituent with Lawesson's reagent

Treatment of sterically crowded thione S-oxides derived from d-camphor with Lawesson's reagent afforded dithiiranes along with deoxygenation of the starting materials, and the mixtures were subjected to mCPBA oxidation to give the corresponding dithiirane S-oxides and thione S-oxides.

Photochemical Oxidation of Thioketones by Singlet Molecular Oxygen Revisited: Insights into Photoproducts, Kinetics, and Reaction Mechanism

Photosensitized oxidation of trimethyl[2.2.1]bicycloheptane thioketones by 1O2 can yield more photoproducts than exclusively ketones and sulfines. Moreover, the ketone/sulfine ratio can be reversed when protic conditions and high thioketone concentrations are used, conversely to earlier results reporting ketones as the main photoproducts. A new mechanistic proposal for sulfine formation is suggested following intermolecular oxygen transfer from a peroxythiocarbonyl intermediate to a second thioketone molecule. Reaction quantum yields (10-5-10-2) depend on the reaction conditions and time. Sulfine production reaches a maximum at short irradiation times, whereas decomposition to the corresponding ketone is observed at long reaction times. When the thioketone substrate has a hydrogen atom at the α position a peroxyvinylsulfenic acid intermediate can be formed by proton transfer. Reaction of this intermediate with another thioketone molecule can yield more sulfine and its tautomeric vinylsulfenic acid, which dimerizes in situ to the thiosulfinate. The hydroperoxyl group of the peroxyvinylsulfenic acid can also rearrange to the α position, and by reaction with the starting thioketone, α-hydroxy thioketone and additional sulfine can be formed, while dehydration yields the α-oxo thioketone. In situ [2 + 2] and [4 + 2] self-cycloaddition of the α-oxo thioketone yields significant amounts of the corresponding adducts at prolonged irradiation times.

Dynamics of capsuleplex formed between octaacid and organic guest molecules - Photophysical techniques reveal the opening and closing of capsuleplex

This manuscript is concerned with the opening and closing of a capsuleplex made up of organic guest molecules and two cavitand molecules known as octaacid (OA). The capsuleplex is loosely held together in water through weak interactions. We have investiga

Synthesis of 14C- and 14C3-labelled Org 37462

Org 37462 (1) is the active ingredient in Orgalutran, an innovative product that reduces the time of treatment in in vitro fertilization from four to less than two weeks. Org 37462 is a synthetic decapeptide containing several amino acids that are unnatur

Expeditious microwave-assisted thionation with the system PSCl 3/H2O/Et3N under solvent-free condition

(Chemical Equation Presented) A novel thionation protocol for carbonyl compounds, with the system PSCl3/H2O/Et3N has been discovered. Clean, rapid, and efficient synthesis of a variety of thiocarbonyl compounds such as thioamides, thiolactams, thioketones, thioxanthones, and thioacridone can be achieved through this simple and convenient method under solventless condition with microwave irradiation.

Asymmetric induction through metalation of chiral dithioacetals and oxathioacetals

The work presented in this article consists of synthesis of chiral dithioacetals and oxathioacetals using pure chiral auxiliaries, such as, (+) camphor, (-) menthol, and L-cysteine. Metalation of these chiral dithioacetals and oxathioacetals, followed by nucleophilic addition to benzaldehyde and removal of chiral auxiliary, furnished scalemic mandelic acid with various enantiomeric purities. Copyright Taylor & Francis Group, LLC.

Synthesis of dithioacetals and oxathioacetals with chiral auxiliaries

One-pot synthesis of dithioacetals as well as an efficient method for oxathioacetal is reported. Additionally, some chiral auxiliaries were used to synthesize enantiomerically pure dithioacetals and oxathioacetals.

A new, efficient and simple method for the thionation of ketones to thioketones using P4S10/Al2O3

A simple, efficient and new method has been developed for the synthesis of thioketones by thionation of ketones using P4S10/Al 2O3 in acetonitrile. It has been found that the P 4S10/Al2O3 combination provides a simple and convenient method for the synthesis of thioketones.